• Bulletin of the Korean Chemical Society
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• v.31 no.10
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• pp.2761-2770
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• 2010

In this study, we have developed QSAR models for a series of 38 piperidine-4-carboxamide CCR5 antagonists using CoMFA, CoMSIA and HQSAR methods. Developed models showed good statistics in terms of $q^2$ and $r^2$ values. Best predictions obtained with standard CoMFA model ($r^2$ = 0.888, $q^2$ = 0.651) and combined CoMSIA model ($r^2$ = 0.892, $q^2$ = 0.665) with electrostatics and H-bond acceptor parameter. The validity of developed models was assessed by test set of 9 compounds, which showed good predictive correlation coefficient for CoMFA (0.804) and CoMSIA (0.844). Bootstrapped analysis showed statistically significant and robust CoMFA (0.968) and CoMSIA (0.936) models. Best HQSAR model was obtained with a $q^2$ of 0.662 and $r^2$ of 0.936 using atom, connection, hydrogen, donor and acceptor as parameters and fragment size (7-10) with optimum number of 6 components. Predictive power of developed HQSAR model was proved by test set and it was found to be 0.728.

• Bulletin of the Korean Chemical Society
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• v.35 no.4
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• pp.1128-1132
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• 2014

A kinetic study on aminolysis of 4-chloro-2-nitrophenyl X-substituted-benzoates (6a-i) in MeCN is reported. The Hammett plot for the reactions of 6a-i with piperidine consists of two intersecting straight lines, while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ${\rho}_X$ = 1.03 and r = 0.78. The nonlinear Hammett plot is not due to a change in rate-determining step (RDS) but is caused by the resonance stabilization of substrates possessing an electron-donating group in the benzoyl moiety. The Br${\phi}$nsted-type plot for the reactions of 4-chloro-2-nitrophenyl benzoate (6e) with a series of cyclic secondary amines is linear with ${\beta}_{nuc}$ = 0.69, an upper limit for reactions reported to proceed through a concerted mechanism. The aminolysis of 6e in aqueous medium has previously been reported to proceed through a stepwise mechanism with a change in RDS on the basis of a curved Br${\phi}$nsted-type plot. It has been concluded that instability of the zwitterionic tetrahedral intermediate ($T^{\pm}$) in MeCN forces the reaction to proceed through a concerted mechanism. This is further supported by the kinetic result that the amines used in this study are less reactive in MeCN than in $H_2O$, although they are more basic in MeCN over 7 $pK_a$ units.

• Journal of Physiology & Pathology in Korean Medicine
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• v.21 no.4
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• pp.940-945
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• 2007

We have examined the induction of HL-60 cell differentiation by treatment of 2-chloromethyl-1-dihydroxyphosphinyl pyrrolidine(2C-1DPP), which is derivative of piperidine and pyrrolidine by ${\alpha}-phosphoramidoakylation$ reaction. It was observed that HL-60 cell proliferation was dose- and time-dependently inhibited by treatment with 2C-1DPP. 2C-1DPP treatment caused a significant change in NBT reduction and enhanced ATRA-induced NBT reduction. Treatment of 2C-1DPP to HL-60 cells increased only CD11b expression in the cells, and also increased markedly G0/G1 stage arrest of HL-60 cells. These results can suggest that 2C-1DPP induced the differentiation of HL-60 cells to granulocytes lineage and enhanced ATRA-induced differentiation. Moreover, DNA expression levels of p27 were up-regulated during 2C-1DPP-dependent HL-60 cell differentiation. Our results suggest that 2C-1DPP have potential as a therapeutic agent in human leukemia.

• Journal of Radiation Industry
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• v.5 no.3
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• pp.221-225
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• 2011

To detect superoxide anion ($O_2{\cdot}^-$) or singlet oxygen ($^1O_2$) in biological systems during gamma irradiation, specific chemical probes, 4,5-dihydroxy-1,3-benzene disulfonic acid (Tiron) or 2,2,6,6-tetramethyl-piperidine (TEMP), were evaluated. Tiron or TEMP spin adducts was structurally stable in aqueous solution during gamma irradiation up to 500 or 1,000 Gy, respectively. The signal of Tiron semiquinone radical, a spin adduct of Tiron upon reaction with $O_2{\cdot}^-$, was slightly increased by gamma irradiation. This trend was dose-dependently manifested in $O_2$-saturated aqueous solution using nitro blue tetrazolium (NBT), a common probe for both hydrated electron ($e{^-}_{aq}$) and $O_2{\cdot}^-$. In contrast, a spin adduct of TEMP, was never inducible by gamma irradiation, while its signal was substantially enhanced by photosensitization of riboflavin. These results suggest that Tiron and NBT or TEMP could be utilized to detect $O_2{\cdot}^-$ or $^1O_2$ in biological systems during gamma irradiation, although $O_2{\cdot}^-$ or $^1O_2$ are not the main reactive oxygen species produced by water radiolysis.

• The Korean Journal of Pesticide Science
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• v.16 no.1
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• pp.1-10
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• 2012

Fungicidal activities against phytopathogenic fungi of diarylthiazole compound of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-fluorophenyl)thiazol-5-yl]-1-methylpiperidine (I) have been determined to be excellent and compound I was used as the leading compounds in this study. Furthermore, the compound was synthesized by reacting them with five functional groups, 4-fluoro-3-methylphenyl, 4-fluoro-3-chlorophenyl, 4-chloro-2-fluorophenyl, 4-bromo-3-methylphenyl and 2,4-dichlorophenyl groups instead of 4-fluorophenyl group. Also, 2-amino-, 2-(N-ethoxycarbonyl)piperidin-4-yl-, and 2-piperidin-4-yl-thiazole were introduced as the leads instead of 2-N-methylpiperidine-4-yl-thiazol of compound I. VIII-1~VIII-5 and XIII-1~XV-5 compounds were newly synthesized and their structures were confirmed by $^1H$-NMR-spectrum. The fungicidal activities of all the synthesized compounds against Phytophthora capsici were examined using the whole plant method. Among the VIII-1~VIII-5 and XIII-1~XV-5 chemicals, XIV-3 showed the most potent antifungal activity in vivo. While the $EC_{50}$ and $EC_{90}$ values of the commercial fungicide dimethomorph and I were $4.26{\pm}0.02$, $14.72{\pm}0.05$ and $1.01{\pm}0.11$, $6.31{\pm}0.09mM$, those of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-chloro-2-fluorophenyl)thiazol-5-yl]-1-methylpiperidine (XIV-3) was $0.98{\pm}0.21$ and $5.85{\pm}0.05mM$. Therefore, XIV-3 can be considered as a viable candidate for the control of plant diseases caused by P. capsici, and further studies will be conducted on the mode of action XIV-3.

• Korean Journal of Environmental Agriculture
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• v.12 no.1
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• pp.27-34
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• 1993

This experiment was conducted to determine the residual amount of dimepiperate (S-1-methyl-1-phenylethyl piperidine-1-carbothioate) and dimepiperate-OH(S-1-methyl-1-phenylethyl-4-hydroxy piperidine-1-carbothioate) in surface water and leachate using a lysimeter system. In surface water, the concentration of dimepiperate was 851-897 ppb in the treatment of 3.0 Kg prod/10a. 1,755-1,781 ppb in the treatment of 6.0 Kg prod/10a 1 day after the treatment. The amount of dimepiperate gradually decreased and was infinitesimal from 35 days after the treatment. In leachate dimepiperate was detected from the 45 days, but its concentration was very low, below 1 ppb, compared to that in surface water. The metabolite of dimepiperate, dimepiperate-OH in surface water was detected after the application of dimepiperate. The highest level of 88-173 ppb occurred 2 day after the treatment of dimepiperate and then decreased gradually. The residual concentration was below 2.13 ppb during 28-63 days. In leachate, the concentration of dimepiperate-OH in the different treatments in the range of 0.5-11 ppb from the 21 days, although each treatment showed different detected date and concentration. The detected concentration showed a little change until 63 days.

• Applied Biological Chemistry
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• v.11
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• pp.173-184
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• 1969

To elucidate the effect of Amo-1618(4-hydroxyl-5-isopropyl-2-methlphenyl trimethyl ammonium chloride, 1-piperidine carboxylate) known as a kind of growth retardant, on the growth, grain yield, increasing the efficiency of nitrogen fertilizer, behavior of mineral nutritions and the rate of phosphorus utilization, this experiment was conducted pot culture method in a vinyl house. Two nitrogen level, namely, practical nitrogen level(1 N) and three times nitrogen level(3 N) was made and labelled double-calcium-superphosphate $Ca(H_2P^{32}O_4)_2.\;2H_2O)$ as a source of radioactive phosphorus(P-32) was employed $80\;{\mu}c/pot$, respectively. Rice seedlings, variety 'Suwon No. 82', was transplanted to a 1/50,000 a china pot on June 13 in 1968. For treatment, at early stage of tillering, 10,000 ppm solution of Amo-1618 was foliar sprayed only one time. The Duncan's new mutiple-range test was adopted for statistical analysis evaluating experimental data at 5% level significance. The results obtained may be summarized as follows; 1) No significant difference was found among the treatments in plant height, but in plot of Amo-1618 treatment and 3 N level, number of tillers was significantly increased than that of others. 2) Weight of 10,000 kernels and seed-setting rate was also remarkably increased in same treatment above. 3) Grain yield per pot was significantly increased in Amo-1618 and 3 N level application. This results seemed to be due to the increased the factors on the yield. 4) Contents of nitrogen and phosphorus per cent in the grain was likewise increased in Amo-1618 and 3 N application. There is, however, no difference among treatments in the content of nitrogen and phosphorus in the leaves and culms of rice plants. 5) On the other hand, the contents of potassium and magnesium, no distinctly tendeny showed among treatments. 6) The rate of phosphorus utilization was significantly increased in the plot of Amo-1618 and 3 N application.

• The Korean Journal of Pesticide Science
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• v.13 no.2
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• pp.63-69
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• 2009

New morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 2(X=O) and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 3(X=C) to which morpholinyl or piperidinyl functional group were introduced at C-4 side chain of the 2-phenylimino-1,3-thiazoline scaffold were synthesized to investigate the effect of NH hydrogen of 2-phenylimino-1,3-thiazoline-4-acetanilide derivatives on the antifungal property against rice blast. Synthesized 30 compounds were screened against 6 kinds of typical plant fungi. Treatment of ketene dimer with chlorine followed by the reaction of morphorine or piperidine without isolation of the intermediate acetoacetylchloride gave $\gamma$-chloro-$\beta$-keto derivatives. These were reacted with thioureas to give morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines respectively in good yield (27-98%). The compound 3j, in which two fluorine atoms are substituted at ortho and para position of phenyl group of 2-phenylimino moiety and piperidinyl group is substituted at C-4, showed the highest antifungal activity (100 ppm, 90%). This result suggested that the substituent at C-4 of the 2-phenylimino-1,3-thiazolines may play a supplementary role to show the antifungal activity against rice blast.

• Korean Journal of Weed Science
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• v.4 no.2
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• pp.169-178
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• 1984

This experiment was conducted to find out selective herbicides which are safe to the rice seedlings and to provide effective weed control method in protected semi-irrigated rice seedbed. There was no crop injury in rice with benzophenap [2-(4-2, 4-dichloro-3-methylbenzoyl)-1, 3-dimethyl-pyrazol-5-yl-oxy)-4'-methyl acetophenone] (240g), pyrazoxyfene [1,3-dimethyl-4-(2,4-dichlorobenzoyl)-Sphenacyloxy pyrazole] (200g), chlormethoxynil [2,4-dichlorophenyl-4-nitro-3-methoxyphenyl ether] (180g), dimepiperate [S-(1-methyl-1-phenethyl)-piperidine-l-carbathioate] (210g), dimepiperate + probenazol [3-allyloxy-1,2-benzisothiazol-1,1-dioxide] (210 + 120g) mixture and dimepiperate + probenazol + molinate [S-ethyl-N,N-hexamethylene-thiol-carbamate] (120 + 120 + 120g) mixture at times of application studied. Butachlor [2-chloro-2',6'-diethyl-N-buthoxymethyl acetanilide] + pyrazolate [4-(2,4-dichlorbenzoyl)-1,3dimethyl-pyrazol-5-yl-p-toluene-sulfonate] (70 + 120g) mixture and butachlor + chlormethoxynil (60 + 120g) mixture caused root length to shorten and root viability to decrease. However, the crop injury was recovered at 25 days after seeding. Benzophenap, pyraxoxyfene and butachlor + pyrazolate mixture were effective for weed control when applied at 2 days before seeding. Chlormethoxynil and butachlor + chlormethoxynil mixture was very effective for controlling annual weed. Dimepiperate, dimepiperate + probenazol mixture and dimepiperate + probenazol + molinate mixture did not control most weeds except for Echinochloa crus-galli (L.) Beauv.

• Korean Journal of Weed Science
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• v.15 no.1
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• pp.46-53
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• 1995

The herbicidal activity of thiocarbamate herbicides and its effect on cell division and elongation were determined. The herbicides studied were molinate(S-ethyl-N,N-hexamethylenethiocarbamate), dimepiperate [S-(${\alpha}$,${\alpha}$-di methylbenzyle)piperidine-1-carbothioate], esprocarb [S-benzyl-N-ethyl-N-(1,2-dimethylpropyl) thiocarbamate], and thiobencarb [S-(4-chlorobenzyl)-N, N-diethylthiocarbamate]. The herbicides applied at the rates ranged from $10^{-6}$ to $10^{-5}M$ did not affect germination and post-germination root growth of rice(Oryza sativa L.) and barnyardgrass [Echinochloa crus-galli(L.) P. Beauv.], but inhibited the post-germination shoot growth. There was no inhibition of gibberellin-induced ${\alpha}$-amylase biosynthesis in de-embryonated rice seeds by the herbicides at $10^{-5}M$, but about 50-60% inhibition occurred at $10^{-4}M$. When the herbicides were applied 7 days after seeding, the rates required to 50% growth inhibition of barnyardgrass were 146g, 91g, 96g, and 102g ai/10a for molinate, dimepiperate, esprocarb, and thiobencarb, respectively. No effect of the herbicides on cell division was found at $10^{-4}M$, but about 31 to 47% inhibition as compared with the untreated check was obtained by treatment of the herbicides at $10^{-3}M$. However, about 33 to 38% inhibition of cell elongation occurred at $10^{-5}M$ of the herbicides. They also inhibited IAA-induced cell elongation.